Specialising in fast sprint finishes, Bennati turned professional in 2002, when he joined the team Acqua & Sapone–Cantina Tollo and wore zebra stripes as part of Mario Cipollini's leadout train.

At the age of 21, Bennati turned professional and joined the Acqua & Sapone–Cantina Tollo team of the successful Italian sprinter Mario Cipollini.

Bennati soon showed an ability to sprint of his own: in March 2002, he finished second in a stage of the Settimana internazionale di Coppi e Bartali, behind Alessandro Petacchi.

In the Grand Tours, Cipollini followed his usual practice of dropping out when the road went up, which gave Bennati a chance to race for himself – he was second to Alessandro Petacchi in one of the stages of the Giro d'Italia.

His first important result was in Gent–Wevelgem, where he outsprinted Thor Hushovd and Fabian Cancellara for 3rd place, behind the breakaway of Nico Mattan and Juan Antonio Flecha.

He did not compete in the Giro d'Italia – where Lampre concentrated on the overall victory with Gilberto Simoni and Damiano Cunego – nor did he ride the Tour de France.

In August, he won three stages and the points jersey in the Tour of Germany, and had good placings in important races such as the Grand Prix de Plouay (4th), the Coppa Placci (5th), and the Giro di Romagna (2nd).

Bennati started the 2006 season with two second places in the Gran Premio della Costa Etruschi (behind Alessandro Petacchi, who had taken over Cipollini's mantle as the dominant Italian sprinter), and then took his first win of the season in February's Volta a la Communitat Valenciana, four seconds ahead of the peloton, led home by Napolitano.

July brought Bennati to his first Tour de France; he was among the top ten finishers in eight stages, including a 2nd place behind McEwen.

Two months later, Bennati returned to the Tour of Poland, where he won two stages and wore the leader's jersey for two days.

Bennati spent much of his off-season training in the Canary Islands (with Daniele Righi, Giuliano Figueras, Caudio Corioni, and Mauro Santambrogio) and began the 2007 racing season with two wins in February.

After a fourth place at the Trofeo Laigueglia, Bennati outsprinted Alessandro Petacchi for three wins in the Volta a la Communidat Valenciana.

In July, Bennati rode in the Tour de France for the second time; he now had enough stature that his goals of winning a stage and competing for the points jersey were considered reasonable.

On the strength of his successes, he was named the leader of the Lampre team for the Vattenfall Cyclassics race, but watched as his teammate Ballan took off from the peloton and held on to win.

Claudio Corioni and Enrico Franzoi, valuable teammates who formed an important part of his leadout train, also signed for Liquigas.

The move to Liquigas brought up some potential frictions: they now had two stars, Bennati and Filippo Pozzato, whose primary targets for the year would be similar.

The next sprinters' stage was the ninth; Bennati won, by a whisker, over Paolo Bettini, who was racing his final Giro d'Italia.

Bennati was not named to the Italian team for the UCI Road World Championships, and his bad luck in Paris–Tours, the sprinters’ classic, continued; he finished 8th in a race won by Philippe Gilbert.

At the Vuelta a España, Bennati took his first win of the 2012 season in a very close finish on stage 18, edging Team Sky's sprinter Ben Swift.

[7] On Saxo–Tinkoff, Bennati managed to be a part of the team for the 2013 Tour de France, even though it was highly occupied by riders like Alberto Contador, Nicolas Roche, Michael Rogers and Roman Kreuziger.